Benzhydryl Compounds
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Benzhydryl Compounds
The benzhydryl compounds are a group of organic compounds whose parent structures include diphenylmethane (which is two benzene rings connected by a single methane), with any number of attached substituents, including bridges. This group typically excludes compounds in which either benzene is fused to another ring (bicyclic, tricyclic, polycyclic) or includes a heteroatom, or where the methane connects to three or four benzenes. The benzhydryl '' radical'' can be abbreviated or Bzh. Carboaromatic Alcohols *''Acyclic:'' pridinol *''Pyrolidino:'' diphenylprolinol *''2-Piperidine:'' pipradrol *''4-Piperidine:'' terfenadine, fexofenadine *''Benzilic ester:'' QNB, JB-336, JB-318, benactyzine Alkenes *''Tricycle:'' amitriptyline, melitracen, cyclobenzaprine, tianeptine, amineptine, clopenthixol, chlorprothixene, flupentixol, thiothixene, zuclopenthixol *''Tricyclic and piperidine:'' pimethixene, cyproheptadine *''Acyclic:'' gilutensin Alkyl(amine)s *''Acyclic:'' (3- ...
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Diphenylmethane2
Diphenylmethane is an organic compound with the chemical formula, formula (C6H5)2CH2 (often abbreviated ). The compound consists of methane wherein two hydrogen atoms are replaced by two phenyl groups. It is a white solid. Diphenylmethane is a common parent structure, skeleton in organic chemistry. The diphenylmethyl group is also known as ''benzhydryl''. Synthesis It is prepared by the Friedel–Crafts alkylation of benzyl chloride with benzene in the presence of a Lewis acid such as aluminium chloride: :C6H5CH2Cl + C6H6 → (C6H5)2CH2 + HCl Reactivity of the C-H bond The methylene group in diphenylmethane is mildly acidic with a pKa, p''K''a of 32.2, and so can be deprotonated with sodium amide. :(C6H5)2CH2 + NaNH2− → (C6H5)2CHNa + NH3 The resulting carbanion can be alkylated. For example, treatment with 1-bromobutane, ''n''-bromobutane produces 1,1-diphenylpentane in 92% yield. :(C6H5)2CH− + CH3CH2CH2CH2Br → (C6H5)2CHCH2CH2CH2CH3 + Br− Alkylation of va ...
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Pipradrol
Pipradrol, also known by its brand name Meratran, is a mild central nervous system stimulant that acts as a norepinephrine-dopamine reuptake inhibitor. Developed in the United States in the 1940s and patented in 1953, pipradrol was initially marketed as an antidepressant in the mid-1950s. It was subsequently used as an adjunct treatment for various conditions, including obesity, senile dementia, narcolepsy, and schizophrenia. Despite its initial promise and relatively mild stimulant effects compared to stronger alternatives, concerns about its abuse potential led to its regulation and withdrawal from widespread use in many countries during the late 1970s. Pipradrol is now classified as a controlled substance in several nations, including the United Kingdom, where it is typically placed in less restrictive drug schedules due to its lower abuse potential compared to other stimulants. Dosage Elixir "Alertonic" with Pipradrol hydrochloride content of 0.044 mg/mL was recommended ...
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Chlorprothixene
Chlorprothixene, sold under the brand name Truxal among others, is a typical antipsychotic of the thioxanthene group. Medical uses Chlorprothixene's principal indications are the treatment of psychotic disorders (e.g. schizophrenia) and of acute mania occurring as part of bipolar disorders. Other uses are pre- and postoperative states with anxiety and insomnia, severe nausea / emesis (in hospitalized patients), the amelioration of anxiety and agitation due to use of selective serotonin reuptake inhibitors for clinical depression, depression and, off-label, the amelioration of Alcohol withdrawal syndrome, alcohol and opioid withdrawal. It may also be used cautiously to treat nonpsychotic irritability, aggression, and insomnia in Pediatrics, pediatric patients. An intrinsic antidepressant effect of chlorprothixene has been discussed, but not proven. Likewise, it is unclear if chlorprothixene has genuine (intrinsic) analgesic effects. However, chlorprothixene can be used as co-med ...
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Clopenthixol
Clopenthixol (Sordinol), also known as clopentixol, is a typical antipsychotic drug of the thioxanthene class. It was introduced by Lundbeck in 1961. Clopenthixol is a mixture of '' cis'' and ''trans'' isomers. Zuclopenthixol, the pure ''cis'' isomer, was later introduced by Lundbeck in 1962, and has been much more widely used. Both drugs are equally effective as antipsychotics and have similar adverse effect profiles, but clopenthixol is half as active on a milligram-to-milligram basis and appears to produce more sedation Sedation is the reduction of irritability or agitation by administration of sedative drugs, generally to facilitate a medical procedure or diagnostic procedure. Examples of drugs which can be used for sedation include isoflurane, diethyl ether, ... in comparison. Clopenthixol is not approved for use in the United States. References External links * Piperazines Chloroarenes Hydroxyethyl compounds Thioxanthene antipsychotics {{ne ...
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Amineptine
Amineptine, formerly sold under the brand name Survector among others, is an atypical antidepressant of the tricyclic antidepressant (TCA) family. It acts as a selective and mixed dopamine reuptake inhibitor and releasing agent, and to a lesser extent as a norepinephrine reuptake inhibitor. Amineptine was developed by the French Society of Medical research in the 1960s. Introduced in France in 1978 by the pharmaceutical company Servier, amineptine soon gained a reputation for abuse due to its short-lived, but pleasant, stimulant effect experienced by some patients. After widespread adoption of this drug, cases of hepatotoxicity emerged, some serious. This, along with the potential for abuse, led to the suspension of the French marketing authorization for Survector in 1999. Amineptine is illegal in both Germany and the United States. Medical uses Amineptine was approved in France for severe clinical depression of endogenous origin in 1978. Contraindications * Chorea * ...
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Tianeptine
Tianeptine, sold under the brand names Stablon, Tatinol, and Coaxil among others, is an atypical tricyclic antidepressant which is used mainly in the treatment of major depressive disorder, although it may also be used to treat anxiety, asthma, and irritable bowel syndrome. Tianeptine has antidepressant and anxiolytic effects with a relative lack of sedative, anticholinergic, and cardiovascular side effects. It has been found to act as an atypical agonist of the μ-opioid receptor with clinically negligible effects on the δ- and κ-opioid receptors. This may explain part of its antidepressant and anxiolytic effects; however, it is thought that tianeptine also modulates glutamate receptors, and this may also explain tianeptine's antidepressant/anxiolytic effects. Tianeptine was discovered and patented by the French Society of Medical Research in the 1960s. It was introduced for medical use in France in 1983. Currently, tianeptine is approved in France and manufactured and m ...
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Cyclobenzaprine
Cyclobenzaprine, sold under several brand names including, historically, Flexeril, is a muscle relaxer used for muscle spasms from musculoskeletal conditions of sudden onset. It is not useful in cerebral palsy. It is taken by mouth. Common side effects include headache, feeling tired, dizziness, and dry mouth. Serious side effects may include an irregular heartbeat. There is no evidence of harm in pregnancy, but it has not been well studied in this population. It should not be used together with MAOIs. How it works is unclear. In any case, it is known to inhibit serotonin and norepinephrine reuptake and to block serotonin, adrenergic, histamine, and muscarinic acetylcholine receptors. Chemically, it is very similar to tricyclic antidepressants like amitriptyline. Cyclobenzaprine was approved for medical use in the United States in 1977. It is available by prescription as a generic medication. In 2022, it was the 45th most commonly prescribed medication in the United ...
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Melitracen
Melitracen (brand names Melixeran, Trausabun) is a tricyclic antidepressant (TCA), for the treatment of depression and anxiety. In addition to single drug preparations, it is also available as Deanxit, marketed by Lundbeck, a combination product containing both melitracen and flupentixol. The pharmacology of melitracen has not been properly investigated and is largely unknown, but it is likely to act in a similar manner to other TCAs. Indeed, melitracen is reported to have imipramine and amitriptyline-like effects and efficacy against depression and anxiety, though with improved tolerability and a somewhat faster onset of action Onset of action is the duration of time it takes for a drug's effects to come to prominence upon administration. With oral administration, it typically ranges anywhere from 20 minutes to over an hour, depending on the drug in question. Other meth .... See also * Fluotracen * Litracen * Dimetacrine References Dimethylamino compounds ...
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Amitriptyline
Amitriptyline, sold under the brand name Elavil among others, is a tricyclic antidepressant primarily used to treat major depressive disorder, and a variety of pain syndromes such as neuropathic pain, fibromyalgia, migraine and tension headaches. Due to the frequency and prominence of side effects, amitriptyline is generally considered a second-line therapy for these indications. The most common side effects are dry mouth, drowsiness, dizziness, constipation, and weight gain. Glaucoma, liver toxicity and abnormal heart rhythms are rare but serious side effects. Blood levels of amitriptyline vary significantly from one person to another, and amitriptyline interacts with many other medications potentially aggravating its side effects. Amitriptyline was discovered in the late 1950s by scientists at Merck and approved by the US Food and Drug Administration (FDA) in 1961. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medicati ...
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Benactyzine
Benactyzine is an anticholinergic drug that was used in the treatment of clinical depression and anxiety disorders before it was pulled from the U.S. market by the FDA due to serious side effects. Its use for these indications was limited by side effects such as dry mouth and nausea, and at high doses it can cause more severe symptoms such as deliriant and hallucinogenic effects. "Large doses of benactyzine in normal subjects may produce a state resembling the action of mescaline or LSD." Brand names have included: Suavitil, Phebex, Phobex, Cedad, Cevanol, Deprol, Lucidil, Morcain, Nutinal, Parasan. While there was some tentative evidence of effectiveness when combined with meprobamate Meprobamate—marketed as Miltown by Wallace Laboratories and Equanil by Wyeth, among others—is a carbamate derivative used as an anxiolytic drug. It was the best-selling minor tranquilizer for a time, but has largely been replaced by the benz ..., with the medication no longer available it i ...
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